Over 50 and Looking for a Job

Team of office workers standing and talking with woman in front, facing camera

Whether you’re feeling age-insecure at your current job, planning a reinvention or trying to get back into the workforce this guide should help.

Getting Started

Getting a job isn’t easy. Especially a good job: a job you enjoy, that pays fairly and with good co-workers and bosses. Those jobs are never in oversupply!

Many people don’t know how to design a job search or even where to start.

Here’s a starting point that actually works. Ask yourself a few deceptively simple questions and write down the answers.

  • What do you want to do? What does your ideal job look like? Which criteria are non-negotiable and which ones are you willing to compromise on?
  • What are you selling? What is your value to a new employer? Warning: it may not be what you think it is.
  • What is the market buying? Read a few relevant job descriptions and write down the attributes the hiring folks are looking for. Do these match the ones you are selling?
  • Finally, is there a viable overlap between what the job you want and the job you can actually get?

How can you tell? If you are getting two good leads a week then you are probably in the right place. If not, you need to expand your target area by location, by role, by seniority, by compensation target, or by industry/domain. Setting too narrow a target is the most basic mistake job-hunters make.

The best channels are usually:

  • Your network of colleagues, friends and acquaintances
  • A few good recruiters (there aren’t many but there are a few). If you scan the job boards for potential roles in your area you’ll probably see a few recruiters multiple times. You can reach out to them, but be aware that many recruiters don’t spend time on folks who reach out to them; they prefer to do the selection and initial reachout themselves.
  • Posted jobs on Monster, Indeed, CareerBuilder and so forth (usually not suitable for senior roles)
  • Approaching companies directly without a specific job in mind; most people never even consider this one

If you are getting adequate lead-flow but repeatedly failing to land a job, perhaps you need to try some new lead channels, try harder in your existing lead channels, or change your approach to the leads you do get.


We all face obstacles in the job hunt. These can be both common problems and problems specific to the older person. Don’t rush to assume that your age is the reason for every obstacle.

One common problem is overspecialization, which often happens in larger companies. Many companies, once they find something you’re good at, keep you at it virtually forever. Remember that one year of experience repeated twenty times doesn’t equal twenty years of experience.

A parallel problem is someone who has stayed at a single company for 15-30 years; fair or not, the perception can be that he/she knows only one way to do the job and isn’t open to new or different approaches.

Older job-seekers sometimes believe that they will be hired because of what they have done. Wrong. You get hired on the basis of what you will do for your new employer.

Many job seekers focus solely on the tasks accomplished (I call it “The What I Done Did Syndrome”), and neglect to highlight the business results. Sure, you were diligent and worked hard, but did your work really impact the business’s success? How? Can you quantify this?

Many also use outdated techniques: long cover letters, wearing a tie to a startup interview, a seven-page resume and other faux pas in today’s world. These details seem minor but they can type you as out of touch and out of date and torpedo your chances.

Many make the mistake of believing what they tell you is the reason you got rejected. Very often the real reason is too loaded for the prospective employer to share, so they make up something to simply make you go away. Don’t overcorrect when the feedback may in fact be an invention!

An Action Plan

  • Understand your pros and cons as a candidate.
  • Craft an impactful resume.
  • Screw the cover letter. People do not read them. Focus on the first half-page of the resume. If this isn’t magnetic, the reader probably will never get to the second page.
  • Prepare carefully for the interview/phone screen.
  • Hone your presentation until it feels natural and you find that people are actually listening.

This article is posted to LinkedIn and also appears on NextForMe (nextforme.com) a fantastic new site developed and operated by old friend Jeff Tidwell, a legend, a luminary and an all around great guy. Check out the other stuff on NextForMe. You’ll be pleased. We guarantee it.